2-Thiocresol → 1-(Cyclopropylsulfanyl)-2-methylbenzene

HRID 70563

反応式

HRID 70563 の反応式
[CH3:1][C:2]([CH3:5])([O-])C.[K+].BrC1CC1.[CH3:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=1[SH:18]>CS(C)=O.[Cl-].[Na+].O>[CH:5]1([S:18][C:13]2[CH:14]=[CH:15][CH:16]=[CH:17][C:12]=2[CH3:11])[CH2:2][CH2:1]1

参加物

6

反応物 3

HCID 87122-ThiocresolHCID 78037BromocyclopropaneHCID 23665647Potassium tert-butoxide

生成物 1

HCID 579565761-(Cyclopropylsulfanyl)-2-methylbenzene

試薬・触媒・溶媒 2

HCID 679Dimethyl Sulfoxide溶媒HCID 57417360Sodium chloride; water溶媒

反応条件

温度
100 °C

実験手順

Potassium t-butoxide (994 mg) and bromocyclopropane (2.92 g) were added to a solution of 2-methylbenzenethiol (1.05 g) in dimethyl sulfoxide (10 mL), and the mixture was stirred at 100° C. for 9.5 hours. The reaction solution was cooled to room temperature and brine was added, followed by extraction with ethyl acetate. The organic layer was dried over anhydrous magnesium sulfate and filtered. The solvent was then evaporated under reduced pressure. The residue was purified by silica gel column chromatography (hexane:ethyl acetate=10:1) to give 1-(cyclopropylsulfanyl)-2-methylbenzene as an orange oil (1.41 g, quant.).

後処理

  1. temperatureThe reaction solution was cooled to room temperature
  2. extractionfollowed by extraction with ethyl acetate
  3. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  4. filtrationfiltered
  5. customThe solvent was then evaporated under reduced pressure
  6. customThe residue was purified by silica gel column chromatography (hexane:ethyl acetate=10:1)

出典と根拠

ORDレコード
ord-53b183a844474fc5ab095796eb2aef6d
出典データセット
uspto-grants-2014_09
特許番号
US08822503B2

関連ノート

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